Trifluoroacetic acid → HCID 21345168, compound

To 2-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from step 121a (469 mg, 1.66 mmol) was added TFA (5 mL) in methylene chloride (5 mL) at 0° C., and the mixture was stirred for 30 minutes. The volatile components were then removed under vacuum. The residue was treated with saturated K2CO3 solution, then extracted with methylene chloride, which was dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluting with chloroform:methanol:NH4OH (10:1:0-10:1:0.5) to afford the free base of the title compound (217 mg). The base (156 mg) was dissolved in methylene chloride (3 mL) and then converted to the salt by treatment with saturated HCl in ether to give the title compound (142 mg). mp 155-156° C. MS (DCI/NH3) m/z 199, 201 (M+H)+, 216 (M+NH4)+. 1H NMR (D2O, 300 MHz) δ2.7-2.79 (m, 2H), 4.13-4.24 (m, 2H), 4.44-4.58 (m, 2H), 4.98 (m, 1H), 7.45 (dd, J=4.8, 8.1 Hz, 1H), 7.59 (dd, J=1.5, 8.2 Hz, 1H), 8.03 (dd, J=1.4, 4.5 Hz, 1H). Anal. Calcd. for C9H11N2OCl.1.0 HCl: C, 45.98; H, 5.14; N, 11.91. Found: C, 45.76; H, 5.09; N, 11.64.

1. customThe volatile components were then removed under vacuum
2. additionThe residue was treated with saturated K2CO3 solution
3. extractionextracted with methylene chloride, which
4. dry with materialwas dried over MgSO4
5. concentrationconcentrated
6. customThe residue was chromatographed on a silica gel column
7. washeluting with chloroform:methanol:NH4OH (10:1:0-10:1:0.5)

ORD record

ord-362c411fe384483cb0a7faca95a6de71

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06403575B1